WO1996025447A1 - Ultraviolet curable epoxidized alkyds - Google Patents
Ultraviolet curable epoxidized alkyds Download PDFInfo
- Publication number
- WO1996025447A1 WO1996025447A1 PCT/US1996/000938 US9600938W WO9625447A1 WO 1996025447 A1 WO1996025447 A1 WO 1996025447A1 US 9600938 W US9600938 W US 9600938W WO 9625447 A1 WO9625447 A1 WO 9625447A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- resin
- fatty acid
- accordance
- alkyd
- anhydride
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/02—Polycondensates containing more than one epoxy group per molecule
- C08G59/027—Polycondensates containing more than one epoxy group per molecule obtained by epoxidation of unsaturated precursor, e.g. polymer or monomer
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/02—Polycondensates containing more than one epoxy group per molecule
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/46—Polyesters chemically modified by esterification
- C08G63/48—Polyesters chemically modified by esterification by unsaturated higher fatty oils or their acids; by resin acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/52—Polycarboxylic acids or polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation
- C08G63/54—Polycarboxylic acids or polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation the acids or hydroxy compounds containing carbocyclic rings
- C08G63/553—Acids or hydroxy compounds containing cycloaliphatic rings, e.g. Diels-Alder adducts
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/91—Polymers modified by chemical after-treatment
- C08G63/914—Polymers modified by chemical after-treatment derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/918—Polycarboxylic acids and polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
- Y10S430/1053—Imaging affecting physical property or radiation sensitive material, or producing nonplanar or printing surface - process, composition, or product: radiation sensitive composition or product or process of making binder containing
- Y10S430/1055—Radiation sensitive composition or product or process of making
- Y10S430/106—Binder containing
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
- Y10S430/1053—Imaging affecting physical property or radiation sensitive material, or producing nonplanar or printing surface - process, composition, or product: radiation sensitive composition or product or process of making binder containing
- Y10S430/1055—Radiation sensitive composition or product or process of making
- Y10S430/106—Binder containing
- Y10S430/109—Polyester
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
- Y10S430/1053—Imaging affecting physical property or radiation sensitive material, or producing nonplanar or printing surface - process, composition, or product: radiation sensitive composition or product or process of making binder containing
- Y10S430/1055—Radiation sensitive composition or product or process of making
- Y10S430/106—Binder containing
- Y10S430/111—Polymer of unsaturated acid or ester
Definitions
- This invention relates to solventless, internally plasticized epoxy compositions which cure rapidly in ultraviolet light.
- a suitable photoinitiator such as triphenylsulfonium hexafluorophosphate [( ⁇ )- 3 S + PF 6 ], is required.
- Sunlight or UV lamps may be used as radiation sources.
- the mechanism of cure is cationic rather than free radical.
- a strong acid HPF 6
- This acid initiates crosslinking through oxirane rings resulting in a network polymer.
- Alkyds are oil modified polyesters. Without oil modification, the polyester is a brittle solid. By incorporating unsaturated fatty acids into the polyester, a film with the desired flexibility can be obtained.
- Alkyds are comprised of an anhydride or diacid, a polyol, and unsaturated fatty acids. Examples of these would be phthalic anhydride, glycerine, and tall oil fatty acid. Vegetable oils, such as soybean oil, contribute both polyol and unsaturated fatty acids to an alkyd formulation. The cure of an alkyd is through autoxidation by a free radical mechanism. The sites of crosslinking are carbons adjacent to unsaturation. Alkyds are one of the most widely used protective coatings due to their durability and relatively low cost. Alkyds typically contain solvents for viscosity reduction.
- epoxy resins are multifunctional glycidyl ethers derived from the reaction of bisphenol A and epichlorhydrin.
- the oxirane rings of these resins react with amine curing agents, such as reactive polyamides, by chemical addition.
- the resulting polymer is widely used in protective coatings when superior corrosion and water resistance is required.
- Solvents are used to reduce the viscosity of the two component reaction mixture.
- Cycloaliphatic epoxy resins such as (3,4 - epoxycyclohexyl) methyl - 3,4 - epoxycyclohexane carboxylate [ ] have previously been employed as solventless epoxy compositions which cure rapidly in ultraviolet light. These resins produce rigid films without the addition of a plasticizer. A flow modifier is typically added to prevent surface defects. Reactive diluents, such as propylene glycol monomethylether, may be added to reduce the viscosity of the formulation.
- Photocopoiymerizable compositions based on epoxy and hydroxyi- containing organic materials were disclosed by Smith in U.S. Patent Number 4,256,828. A process for this polymerization was disclosed by Smith in U.S. Patent Number 4,318,766. Crivello discussed the use of a hydroxy functional flexibilizer in U.S. Patent Number 4,175,972. These patents also involved the use of photosensitive aromatic sulfonium salts. Simultaneous free radical and cationic cure of mixtures of certain oxirane containing and aliphatically unsaturated containing organic resins was addressed by Crivello in U.S. Patent Number 4,245,029.
- Arylsulfonium salt- solvent mixtures were disclosed as photoinitiators by Crivello in U.S. Patent Number 4,273,668. Propylene carbonate was specifically identified as a solvent. Additional photoinitiators were identified by Crivello in U.S. Patent Numbers 4,407,759 and 4,41 7,061 . General structures for these photoinitiators are
- epoxidized alkyd prepared from tall oil fatty acid, glycerine, and tetrahydrophthalic anhydride (THPA) is illustrated as follows:
- a suitable photoinitiator such as triphenyl sulfonium hexafluor ⁇ ophosphate
- a suitable photoinitiator is mixed with the epoxy resin at a concentration of 3% by weight. This mixture is stable in the absence of UV light.
- a photon strikes the photoinitiator, a strong acid is generated which initiates rapid cationic cure through the oxirane rings of the epoxy resin.
- TOFA tall oil fatty acid
- ACINTOL ® EPG from Arizona Chemical Company
- WFE wiped film evaporator
- Oleic acid such as EMERSOL ® 221 from the Emery Industries Division of Henkel
- Glycerine is the preferred polyol of this invention. Trimethylolpropane can be used when a more flexible coating is desired, although a slower cure rate is obtained. Stoichiometric amounts of polyols and acids are used to form the alkyd.
- a preferred anhydride of this invention is 1 ,2,3,6-tetrahydrophthalic anhydride.
- the intended applications for this invention are those in which the epoxy resin viscosity can be reduced by heat or by a reactive diluent, such as limonene dioxide.
- a reactive diluent such as limonene dioxide.
- An example would be the coating of optical fibers.
- Another example would be protective coatings applied by thermal spraying.
- Equipment 500 ml, 3 neck flask equipped with an agitator, nitrogen inlet thermometer with thermowatch, steam heated precondenser, distilla ⁇ tion head with * thermometer, water cooled condenser, vacuum adapter, receiver, vacuum apparatus, heating mantle, and bubble trap .
- Equipment 500 ml, 3 neck flask equipped with an agitator, nitrogen inlet thermometer with thermowatch, steam heated precondenser, distillation head with thermometer, water cooled condenser, vacuum adapter, receiver, vacuum apparatus, heating mantle, and bubble trap.
- Epoxidation of the alkyds of this invention can be accomplished as follows:
- Equipment 500 ml, 3 neck flask with agitator, N 2 inlet, thermometer with thermowatch, equilibrium addition funnel, ice bath, heating mantle, bubble trap, and separatory funnels.
- a 3 mil film was drawn on a cold rolled steel panel with a draw down bar. The film was placed in direct sunlight.
- LDO Limonene Dioxide
- Viscosity 25 2 C 31,300 cps 4,060 cps Viscosity, 40 2 C 7,560 cps 1,350 cps
- TMP trimethylolpropane
- TMP Trimethylolpropane
- MTHPA methyl tetrahydrophthalic anhydride
Abstract
Description
Claims
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
MX9706220A MX9706220A (en) | 1995-02-15 | 1996-02-06 | Ultraviolet curable epoxidized alkyds. |
AU47655/96A AU4765596A (en) | 1995-02-15 | 1996-02-06 | Ultraviolet curable epoxidized alkyds |
EP96903643A EP0809665A4 (en) | 1995-02-15 | 1996-02-06 | Ultraviolet curable epoxidized alkyds |
JP8524955A JPH11501957A (en) | 1995-02-15 | 1996-02-06 | UV curable epoxidized alkyds |
CA002208853A CA2208853C (en) | 1995-02-15 | 1996-02-06 | Ultraviolet curable epoxidized alkyds |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US08/388,926 | 1995-02-15 | ||
US08/388,926 US5612445A (en) | 1995-02-15 | 1995-02-15 | Ultraviolet curable epoxidized alkyds |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1996025447A1 true WO1996025447A1 (en) | 1996-08-22 |
Family
ID=23536108
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US1996/000938 WO1996025447A1 (en) | 1995-02-15 | 1996-02-06 | Ultraviolet curable epoxidized alkyds |
Country Status (7)
Country | Link |
---|---|
US (2) | US5612445A (en) |
EP (1) | EP0809665A4 (en) |
JP (1) | JPH11501957A (en) |
AU (1) | AU4765596A (en) |
CA (1) | CA2208853C (en) |
MX (1) | MX9706220A (en) |
WO (1) | WO1996025447A1 (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1998042766A1 (en) * | 1997-03-21 | 1998-10-01 | Lonza S.P.A. | Cycloaliphatic epoxy resins |
US7410044B2 (en) | 2003-01-31 | 2008-08-12 | Anzpac Systems Limited | Article carrier for a grading apparatus |
Families Citing this family (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6632859B1 (en) | 1999-03-17 | 2003-10-14 | Raymond H. Jones | Alkyd-based ink vehicles and ink compositions |
MXPA02006937A (en) * | 2000-01-14 | 2004-11-12 | Abb Power T & D Co | Transparent epoxy structures. |
ITMI20010259A1 (en) * | 2001-02-09 | 2002-08-09 | Lonza Spa | SOLID OXYDRYLATED CYCLOALIPHATIC EPOXY RESINS PROCEDURE FOR THE PREPARATION AND COMPOSITIONS OF COATED POWDER PAINTS |
US6706404B2 (en) | 2001-06-26 | 2004-03-16 | Strathmore Products, Inc. | Radiation curable composition |
JP3469567B2 (en) * | 2001-09-03 | 2003-11-25 | 三菱電機株式会社 | Acoustic encoding device, acoustic decoding device, acoustic encoding method, and acoustic decoding method |
US7001667B2 (en) * | 2002-07-17 | 2006-02-21 | Ppg Industries Ohio, Inc. | Alkyd-based free radical wood coating compositions |
US6794055B2 (en) | 2003-02-03 | 2004-09-21 | Ppg Industries Ohio, Inc. | Alkyd-based free radical cured wood stains |
US7691946B2 (en) * | 2005-09-30 | 2010-04-06 | The United States Of America As Represented By The Secretary Of Agriculture | Soy-based thermosensitive hydrogels for controlled release systems |
AU2010216379A1 (en) * | 2009-02-20 | 2011-09-15 | Encore Rail Systems, Inc. | Methods for repair and preventative maintenance of railroad ties using UV curable polymers |
DE102009049479A1 (en) * | 2009-06-08 | 2010-12-09 | Sms Siemag Ag | Integration of an optical waveguide of a measuring sensor into a component |
KR102007046B1 (en) * | 2011-01-26 | 2019-08-02 | 나믹스 가부시끼가이샤 | Electroconductive paste and method for manufacturing same |
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US3673140A (en) * | 1971-01-06 | 1972-06-27 | Inmont Corp | Actinic radiation curing compositions and method of coating and printing using same |
US4131579A (en) * | 1976-08-24 | 1978-12-26 | Hoechst Aktiengesellschaft | Low-viscosity air-drying alkyd resins |
US4474941A (en) * | 1982-12-16 | 1984-10-02 | Henkel Kommanditgesellschaft Auf Aktien | Alkyd resins containing functional epoxides |
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-
1995
- 1995-02-15 US US08/388,926 patent/US5612445A/en not_active Expired - Lifetime
-
1996
- 1996-02-06 WO PCT/US1996/000938 patent/WO1996025447A1/en not_active Application Discontinuation
- 1996-02-06 EP EP96903643A patent/EP0809665A4/en not_active Withdrawn
- 1996-02-06 JP JP8524955A patent/JPH11501957A/en active Pending
- 1996-02-06 CA CA002208853A patent/CA2208853C/en not_active Expired - Fee Related
- 1996-02-06 AU AU47655/96A patent/AU4765596A/en not_active Abandoned
- 1996-02-06 MX MX9706220A patent/MX9706220A/en unknown
- 1996-12-09 US US08/762,251 patent/US5821324A/en not_active Expired - Lifetime
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3673140A (en) * | 1971-01-06 | 1972-06-27 | Inmont Corp | Actinic radiation curing compositions and method of coating and printing using same |
US4131579A (en) * | 1976-08-24 | 1978-12-26 | Hoechst Aktiengesellschaft | Low-viscosity air-drying alkyd resins |
US4474941A (en) * | 1982-12-16 | 1984-10-02 | Henkel Kommanditgesellschaft Auf Aktien | Alkyd resins containing functional epoxides |
Non-Patent Citations (1)
Title |
---|
See also references of EP0809665A4 * |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1998042766A1 (en) * | 1997-03-21 | 1998-10-01 | Lonza S.P.A. | Cycloaliphatic epoxy resins |
US7410044B2 (en) | 2003-01-31 | 2008-08-12 | Anzpac Systems Limited | Article carrier for a grading apparatus |
Also Published As
Publication number | Publication date |
---|---|
US5821324A (en) | 1998-10-13 |
JPH11501957A (en) | 1999-02-16 |
EP0809665A4 (en) | 1998-05-20 |
US5612445A (en) | 1997-03-18 |
EP0809665A1 (en) | 1997-12-03 |
CA2208853C (en) | 2002-04-30 |
MX9706220A (en) | 1997-12-31 |
AU4765596A (en) | 1996-09-04 |
CA2208853A1 (en) | 1996-08-22 |
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